Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound

ABSTRACT

wherein in Formula 1, A1 to A4, M, and T1 to T3 are the same as described in the specification.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to Korean Patent Application No.10-2017-0063625, filed on May 23, 2017, in the Korean IntellectualProperty Office, and all the benefits accruing therefrom under 35 U.S.C.§ 119, the content of which is incorporated herein in its entirety byreference.

BACKGROUND 1. Field

One or more embodiments relate to an organometallic compound, an organiclight-emitting device including the organometallic compound, and adiagnostic composition including the organometallic compound.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices, whichhave superior characteristics in terms of a viewing angle, a responsetime, a brightness, a driving voltage, and a response speed, and whichproduce full-color images.

In an example, an organic light-emitting device includes an anode, acathode, and an organic layer disposed between the anode and thecathode, wherein the organic layer includes an emission layer. A holetransport region may be disposed between the anode and the emissionlayer, and an electron transport region may be disposed between theemission layer and the cathode. Holes provided from the anode may movetoward the emission layer through the hole transport region, andelectrons provided from the cathode may move toward the emission layerthrough the electron transport region. The holes and the electronsrecombine in the emission layer to produce excitons. These excitonstransit from an excited state to a ground state, thereby generatinglight.

Meanwhile, luminescent compounds may be used to monitor, sense, ordetect a variety of biological materials including cells and proteins.An example of the luminescent compounds includes a phosphorescentluminescent compound.

Various types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

Aspects of the present disclosure provide an organometallic compound, anorganic light-emitting device including the organometallic compound, anda diagnostic composition including the organometallic compound.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

An aspect of the present disclosure provides an organometallic compoundrepresented by Formula 1:

M in Formula 1 may be beryllium (Be), magnesium (Mg), aluminum (Al),calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu),zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru),rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt),or gold (Au), in Formula 1, two bonds selected from a bond between A₁and M, a bond between A₂ and M, a bond A₃ and M, and a bond between A₄and M may each be a covalent bond, and the others thereof may each be acoordinate bond,

A₁ in Formula 1 may be ring CY₁ represented by Formula A1-1 or A1-2, andin Formulae A1-1 and A1-2, * indicates a binding site to M in Formula 1,and *′ indicates a binding site to T₁ in Formula 1,

A₂ in Formula 1 may be ring CY₂ represented by one of Formulae A2-1 toA2-3, and in Formulae A2-1 to A2-3, * indicates a binding site to M inFormula 1, *′ indicates a binding site to T₁ in Formula 1, and *″indicates a binding site to T₂ in Formula 1,

A₃ in Formula 1 may be ring CY₃ represented by one of Formulae A3-1 toA3-3, and in Formulae A3-1 to A3-3, * indicates a binding site to M inFormula 1, *″ indicates a binding site to T₂ in Formula 1, and *′indicates a binding site to T₃ in Formula 1,

A₄ in Formula 1 may be a first atom linked to M, or a non-cyclic moietyincluding the first atom linked to M,

the first atom may be B, P, Si, O, or S,

X₁ to X₃ and Y₁ to Y₆ in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 toA3-3 may each independently be C or N,

rings CY₁ to CY₃ in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3may each independently be a C₅-C₃₀ carbocyclic group or a C₁-C₃₀heterocyclic group,

T₁ to T₃ in Formula 1 may each independently be selected from a singlebond, a double bond, *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′,*—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′,*—S(═O)—*′, *—S(═O)₂—*′, *—C(R₇)═*′, *═C(R₇)—*′, *—C(R₇)═C(R₈)—*′,*—C(═S)—*′, and *—C≡C—*′, and * and *′ each indicated a binding site toa neighboring atom,

R₇ and R₈ may optionally be linked via a single bond, a double bond, ora first linking group to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup,

R₁ to R₃, R₇, and R₈ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉),

a1 to a3 in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 may eachindependently be an integer from 0 to 20,

two of a plurality of neighboring groups R₁ may optionally be linked toform a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₃₀ heterocyclic group,

two of a plurality of neighboring groups R₂ may optionally be linked toform a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₃₀ heterocyclic group,

two of a plurality of neighboring groups R₃ may optionally be linked toform a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₃₀ heterocyclic group,

two or more groups selected from R₁ to R₃ may optionally be linked toform a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₃₀ heterocyclic group,

A₁ and A₄ in Formula 1 are not linked to each other, Formula 1 satisfiesat least one of a “First Condition” to a “Third Condition”:

“First Condition”

A₁ in Formula 1 is represented by Formula A1-2,

“Second Condition”

A₂ in Formula 1 is represented by Formula A2-2 or A2-3, and

“Third Condition”

A3 in Formula 1 is represented by Formula A3-2 or A3-3,

at least one substituent of the substituted C₅-C₃₀ carbocyclic group,the substituted C₁-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₆₀ alkoxy group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅),—B(Q₁₆)(Q₁₇), and —P(═O)(Q₁₈)(Q₁₉);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁—C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), and —P(═O)(Q₂₈)(Q₂₉);and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), and —P(═O)(Q₃₈)(Q₃₉),and

Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkyl group substituted with atleast one elected from deuterium, a C₁-C₆₀ alkyl group, and a C₆-C₆₀aryl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁—C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryl group substituted with at least onedeuterium, a C₁-C₆₀ akyl group, and a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group.

Another aspect of the present disclosure provides an organiclight-emitting device including:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the secondelectrode

wherein the organic layer includes an emission layer and at least one ofthe above organometallic compounds.

The organometallic compounds may act as a dopant in the organic layer.

Another aspect of the present disclosure provides a diagnosticcomposition including at least one organometallic compound representedby Formula 1.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the FIGURE which is a schematic view of an organiclight-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the figures, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” It will be further understood that theterms “comprises” and/or “comprising,” or “includes” and/or “including”when used in this specification, specify the presence of statedfeatures, regions, integers, steps, operations, elements, and/orcomponents, but do not preclude the presence or addition of one or moreother features, regions, integers, steps, operations, elements,components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

An organometallic compound according to an embodiment is represented byFormula 1 below:

M in Formula 1 may be beryllium (Be), magnesium (Mg), aluminum (Al),calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu),zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru),rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt),or gold (Au).

In an embodiment, M may be Pd or Pt, but embodiments of the presentdisclosure are not limited thereto.

In Formula 1, two bonds selected from a bond between A₁ and M, a bondbetween A₂ and M, a bond between A₃ and M, and a bond between A₄ and Mmay each be a covalent bond, and the other bonds may each be acoordinate bond. Therefore, the organometallic compound represented byFormula 1 may be electrically neutral.

In an embodiment, a bond between A₁ and M and a bond between A₄ and Mmay each be a covalent bond, and a bond between A₂ and M and a bondbetween A₃ and M may each be a coordinate bond.

A₁ in Formula 1 may be ring CY₁ represented by Formula A1-1 or A1-2, andin Formulae A1-1 and A1-2, * indicates a binding site to M in Formula 1,and *′ indicates a binding site to T₁ in Formula 1; A₂ in Formula 1 maybe ring CY₂ represented by one of Formulae A2-1 to A2-3, and in FormulaeA2-1 to A2-3, * indicates a binding site to M in Formula 1, *′ indicatesa binding site to T₁ in Formula 1, and *″ indicates a binding site to T₂in Formula 1; A₃ in Formula 1 may be ring CY₃ represented by one ofFormulae A3-1 to A3-3, and in Formulae A3-1 to A3-3, * indicates abinding site M in Formula 1, *″ indicates a binding site to T₂ inFormula 1, and *′ indicates a binding site to T₃ in Formula 1; and A₄ inFormula 1 may be a first atom linked to M, or a non-cyclic moietyincluding the first atom linked to M:

The first atom may be, for example, B, P, Si, O, or S, but embodimentsof the present disclosure are not limited thereto.

In an embodiment, the first atom may be O, but embodiments of thepresent disclosure are not limited thereto.

X₁ to X₃ and Y₁ to Y₆ in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 toA3-3 may each independently be C or N.

For example, X₁ to X₃ in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 toA3-3 may each be N, but embodiments of the present disclosure are notlimited thereto.

Rings CY₁ to CY₃ in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3may each independently be a C₅-C₃₀ carbocyclic group or a C₁-C₃₀heterocyclic group.

For example, rings CY₁ to CY₃ may each independently be selected from abenzene group, a naphthalene group, an anthracene group, a phenanthrenegroup, a triphenylene group, a pyrene group, a chrysene group, acyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a furangroup, a thiophene group, a silole group, an indene group, a fluorenegroup, an indole group, a carbazole group, a benzofuran group, adibenzofuran group, a benzothiophene group, a dibenzothiophene group, abenzosilole group, a dibenzosilole group, an azafluorene group, anazacarbazole group, an azadibenzofuran group, an azadibenzothiophenegroup, an azadibenzosilole group, a pyridine group, a pyrimidine group,a pyrazine group, a pyridazine group, a triazine group, a quinolinegroup, an isoquinoline group, a quinoxaline group, a quinazoline group,a phenanthroline group, a pyrrole group, a pyrazole group, an imidazolegroup, a triazole group, an oxazole group, an isoxazole group, athiazole group, an isothiazole group, an oxadiazole group, a thiadiazolegroup, a benzopyrazole group, a benzimidazole group, a benzoxazolegroup, a benzothiazole group, a benzoxadiazole group, a benzothiadiazolegroup, a 5,6,7,8-tetrahydroisoquinoline group, a5,6,7,8-tetrahydroquinoline group, and a benzocarbazole group.

In one or more embodiments, rings CYC to CY3 may each independently bei) a 5-membered ring, ii) a 6-membered ring, iii) a condensed ring withtwo or more 6-membered rings, or iv) a condensed ring with at least one5-membered ring and at least one 6-membered ring; the 5-membered ringmay be selected from a cyclopentadiene group, a furan group, a thiophenegroup, a pyrrole group, a silole group, an oxazole group, an isoxazolegroup, an oxadiazole group, an isoxadiazole group, an oxatriazole group,an isoxatriazole group, a thiazole group, an isothiazole group, athiadiazole group, an isothiadiazole group, a thiatriazole group, anisothiatriazole group, a pyrazole group, an imidazole group, a triazolegroup, a tetrazole group, an azasilole group, a diazasilole group, and atriazasilole group; and the 6-membered ring may be selected from acyclohexane group, a cyclohexene group, an admantane group, a norbornanegroup, a norbornene group, a benzene group, a pyridine group, apyrimidine group, a pyrazine group, a pyridazine group, and a triazinegroup.

In an embodiment, at least one of rings CY₁ to CY₃ may be a condensedring with two or more 6-membered rings or a condensed ring with at leastone 5-membered ring and at least one 6-membered ring. The 5-memberedring and the 6-membered ring are the same as described above.

In an embodiment, when A₁ is the condensed ring with at least one5-membered ring and at least one 6-membered ring, the 5-membered ring inthe condensed ring may be linked to T₁ in Formula 1.

In one or more embodiments, when A₁ is the condensed ring with at leastone 5-membered ring and at least one 6-membered ring, the 6-memberedring in the condensed ring may be linked to T₁ in Formula 1.

In one or more embodiments, when A2 is the condensed ring with at leastone 5-membered ring and at least one 6-membered ring, the 5-memberedring in the condensed ring may be linked to T₁ in Formula 1.

In one or more embodiments, when A2 is the condensed ring with at leastone 5-membered ring and at least one 6-membered ring, the 6-memberedring in the condensed ring may be linked to T₁ in Formula 1.

The non-cyclic moiety including the first atom linked to M may be*—B(R₄₁)—*′, P(R₄₁)—*′, *—Si(R₄₁)(R₄₂)—*′, *—B(R₄₁)—C(═O)—*′,*—P(R₄₁)—C(═O)—*′, *—Si(R₄₁)(R₄₂)—C(═O)—*′, *—O—C(═O)—*′, or*—S—C(═O)—*′ (wherein R₄₁ and R₄₂ are the same as described inconnection with R₄, * indicates a binding site to M in Formula 1, and *′indicates a binding site to T₃ in Formula 1), but embodiments of thepresent disclosure are not limited thereto.

T₁ to T₃ in Formula 1 may each independently be selected from a singlebond, a double bond, *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′,*—Si(R₇)(R₈)—*40 , *—Ge(R₇)(R₈)—*—S—*′, *—Se—*′, *—C(═O)—*′, *—S(═O)—*′,*—S(═O)₂-*′, *—C(R₇)═*′, *═C(R₇)—*′, *—C(R₇)═C(R₈)—*′, *—C(═S)—*′, and*—C≡C—*′. * and *′ each indicate a binding site to a neighboring atom.R₇ and R₈ are the same as described above, and R₇ and R₈ may optionallybe linked via a single bond, a double bond, or a first linking group toform a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₃₀ heterocyclic group.

The first linking group may be selected from *—N(R₉)—*′, *—B(R₉)—*′,*—P(R₉)—*′, *—C(R₉)(R₁₀)—*′, *—Si(R₉)(R₁₀)—*′, *—Ge(R₉)(R₁₀)—*′,*—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂-*′, *—C(R₉)═*′,*═C(R₉)—*′, *—C(R₉)═C(R₁₀)—*′, *—C(═S)—*′, and *—C≡C—*′, R₉ and R₁₀ arethe same as described in connection with R₇, and * and *′ each indicatea binding site to a neighboring atom.

In an embodiment, T₁ and T₂ may each be a single bond.

R₁ to R₃, R₇, and R₈ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—N(Q₁(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉).

For example, R₁ to R₃, R₇, and R₈ may each independently be selectedfrom:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,—SF₅, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂,—CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a fluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅); and

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉), and

Q₁ to Q₉ and Q₃₃ to Q₃₅ may each independently be selected from:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃,—CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, and —CD₂CDH₂;

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butylgroup, a sec-butyl group, a tert-butyl group, an n-pentyl group, aniso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenylgroup, and a naphthyl group; and an n-propyl group, an iso-propyl group,an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butylgroup, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, atert-pentyl group, a phenyl group, and a naphthyl group, eachsubstituted with at least one selected from deuterium, a C₁-C₁₀ alkylgroup, and a phenyl group.

In an embodiment, R₁ to R₃, R₇, and R₈ may each independently beselected from hydrogen, deuterium, —F, a cyano group, a nitro group,—SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, groups representedby Formulae 9-1 to 9-19, groups represented by Formulae 10-1 to 10-156,-N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q9) (wherein Q1to Q9 are the same as described herein), but embodiments of the presentdisclosure are not limited thereto:

In Formulae 9-1 to 9-19 and 10-1 to 10-156, “Ph” indicates a phenylgroup, “TMS” indicates a trimethylsilyl group, and “*” indicates abinding site to a neighboring atom.

a1, a2, and a3 in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3respectively indicate the number of groups R₁, the number of groups R₂,and the number of groups R₃, and may each independently be an integerfrom 0 to 20 (for example, 0, 1, 2, 3, or 4). When a1 is two or more,two or more groups R₁ may be identical to or different from each other,when a2 is two or more, two or more groups R₂ may be identical to ordifferent from each other, and when a3 is two or more, two or moregroups R₃ may be identical to or different from each other.

i) Two of a plurality of neighboring groups R₁ in Formulae A1-1 and A1-2may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup, ii) two of a plurality of neighboring groups R₂ in Formulae A2-1to A2-3 may optionally be linked to form a substituted or unsubstitutedC₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, iii) two of a plurality of neighboring groups R₃ inFormulae A3-1 to A3-3 may optionally be linked to form a substituted orunsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstitutedC₁-C₃₀ heterocyclic group, and iv) two or more groups selected from R₁to R₃ in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 mayoptionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup.

For example, i) a substituted or unsubstituted C₅-C₃₀ carbocyclic groupor a substituted or unsubstituted C₁-C₃₀ heterocyclic group, formed bylinking two of a plurality of neighboring groups R₁ in Formulae A1-1 andA1-2, ii) a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₃₀ heterocyclic group, formed bylinking two of a plurality of neighboring groups R₂ in Formulae A2-1 toA2-3, iii) a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₃₀ heterocyclic group, formed bylinking two of a plurality of neighboring groups R₃ in Formulae A3-1 toA3-3, and iv) a substituted or unsubstituted C₅-C₃₀ carbocyclic group ora substituted or unsubstituted C₁-C₃₀ heterocyclic group, formed bylinking two neighboring groups selected from R₁ to R₃ in Formulae A1-1,A1-2, A2-1 to A2-3, and A3-1 to A3-3 may each independently be selectedfrom:

a pentadiene group, a cyclohexane group, a cycloheptane group, anadamantane group, a bicycloheptane group, a bicyclo-octane group, abenzene group, a pyridine group, a pyrimidine group, a pyrazine group, apyridazine group, a naphthalene group, an anthracene group, a tetracenegroup, a phenanthrene group, a dihydronaphthalene group, a phenalenegroup, a benzothiophene group, a benzofuran group, an indene group, anindole group, a benzosilole group, an azabenzothiophene group, anazabenzofuran group, an azaindene group, an azaindole group, and anazabenzosilole group;

a pentadiene group, a cyclohexane group, a cycloheptane group, anadamantane group, a bicycloheptane group, a bicyclo-octane group, abenzene group, a pyridine group, a pyrimidine group, a pyrazine group, apyridazine group, a naphthalene group, an anthracene group, a tetracenegroup, a phenanthrene group, a dihydronaphthalene group, a phenalenegroup, a benzothiophene group, a benzofuran group, an indene group, anindole group, a benzosilole group, an azabenzothiophene group, anazabenzofuran group, an azaindene group, an azaindole group, and anazabenzosilole group, each substituted with at least one R_(10a),

but embodiments of the present disclosure are not limited thereto.

R_(10a) is the same as described in connection with R₁.

“An azabenzothiophene group, an azabenzofuran group, an azaindene group,an azaindole group, an azabenzosilole group, an azadibenzothiophenegroup, an azadibenzofuran group, an azafluorene group, an azacarbazolegroup, and an azadibenzosilole group” as used herein meanheteroatom-containing rings that respectively have the same structure as“a benzothiophene group, a benzofuran group, an indene group, an indolegroup, an benzosilole group, a dibenzothiophene group, a dibenzofurangroup, a fluorene group, a carbazole group, and a dibenzosilole group”,except that at least one of carbons forming the rings thereof issubstituted with nitrogen.

A₁ and A₄ in Formula 1 are not linked to each other. That is, theorganometallic compound represented by Formula 1 may have threecyclometallated rings sharing M with one another.

Formula 1 satisfies at least one of a “First Condition” to a “ThirdCondition” below:

“First Condition”

A₁ in Formula 1 is represented by Formula A1-2,

“Second Condition”

A₂ in Formula 1 is represented by Formula A2-2 or A2-3, and

“Third Condition”

A₃ in Formula 1 is represented by Formula A3-2 or A3-3.

For example, Formula 1 may satisfy the “First Condition” and the “SecondCondition”.

In an embodiment, Formula 1 may satisfy all of the “First Condition” tothe “Third Condition”.

In an embodiment, A₁ in Formula 1 may be represented by one of FormulaeA1-1(1) to A1-1(26) and A1-2(1) to A1-2(74):

In Formulae A1-1(1) to A1-1(26) and Al -2(1) to A1-2(74),

X₁ and R₁ are each independently the same as described herein,

X₁₁ may be O, S, N(R₁₁), C(R₁₁)(R₁₂), or Si(R₁₁)(R₁₂),

X₁₃ may be N or C(R₁₃),

X₁₄ may be N or C(R₁₄),

R₁₁ to R₁₈ are each independently the same as described in connectionwith R₁,

a17 may be an integer from 0 to 7,

a16 may be an integer from 0 to 6,

a15 may be an integer from 0 to 5,

a14 may be an integer from 0 to 4,

a13 may be an integer from 0 to 3,

a12 may be an integer from 0 to 2,

* indicates a binding site to M in Formula 1, and

*′ indicates a binding site to T₁ in Formula 1.

In one or more embodiments, A₂ in Formula 1 may be represented by one ofFormulae A2-1(1) to A2-1(17), A2-2(1) to A2-2(58), and A2-3(1) toA2-3(58):

In Formulae A2-1(1) to A2-1(17), A2-2(1) to A2-2(58), and A2-3(1) toA2-3(58),

X₂ and R₂ are each independently the same as described herein,

X₂₁ may be O, S, N(R₂₁), C(R₂₁)(R₂₂), or Si(R₂₁)(R₂₂),

X₂₃ may be N or C(R₂₃),

X₂₄ may be N or C(R₂₄),

R₂₁ to R₂₈ are each independently the same as described in connectionwith R₂,

a26 may be an integer from 0 to 6,

a25 may be an integer from 0 to 5,

a24 may be an integer from 0 to 4,

a23 may be an integer from 0 to 3,

a22 may be an integer from 0 to 2,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to T₁ in Formula 1, and

*″ indicates a binding site to T₂ in Formula 1.

In one or more embodiments, A₃ in Formula 1 may be represented by one ofFormulae A3-1(1) to A3-1(21), A3-2(1) to A3-2(58), and A3-3(1) toA3-3(58):

In Formulae A3-1(1) to A3-1(21), A3-2(1) to A3-2(58), and A3-3(1) toA3-3(58),

X₃ and R₃ are each independently the same as described herein,

X₃₁ may be O, S, N(R₃₁), C(R₃₁)(R₃₂), or Si(R₃₁)(R₃₂),

X₃₃ may be N or C(R₃₃),

X₃₄ may be N or C(R₃₄),

R₃₁ to R₃₈ are each independently the same as described in connectionwith R₃,

a36 may be an integer from 0 to 6,

a35 may be an integer from 0 to 5,

a34 may be an integer from 0 to 4,

a33 may be an integer from 0 to 3,

a32 may be an integer from 0 to 2,

* indicates a binding site to M in Formula 1,

*′ indicates a binding site to T₂ in Formula 1, and

*″ indicates a binding site to T₃ in Formula 1.

In one or more embodiments,

i) A₄ may be *—O—*′ or *—S—*′, and T₃ may be *—N(R₇)—*′, *—B(R₇)—*′,*—C(R₇)(R₈)—*′, *—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′, or *—C(═O)—*′;

ii) A₄ may be represented by one of Formulae 4(1) to 4(5), and T₃ may bea single bond, or

iii) A₄ may be *—O—*′, or *—S—*′, and T₃ may be a single bond, butembodiments of the present disclosure are not limited thereto:

In Formulae A4(1) to A4(5),

R₄₁ and R₄₂ are each independently the same as described in connectionwith R₁,

* indicates a binding site to M in Formula 1, and

*′ indicates a binding site to T₃ in Formula 1.

In one or more embodiments,

A₁ in Formula 1 may be represented by one of Formulae CY1-1 to CY1-11,and/or

A₂ in Formula 1 may be represented by one of Formulae CY2-1 to CY2-5,and/or

A₃ in Formula 1 may be represented by one of Formulae CY3-1 to CY3-10:

In Formulae CY1-1 to CY1-11, CY2-1 to CY2-5, and CY3-1 to CY3-10,

X₂, X₃, and R₁ to R₃ are each independently the same as describedherein,

R_(1a) and R_(1b) are each independently the same as described inconnection with R₁,

X₂₁ may be O, S, N(R₂₁), C(R₂₁)(R₂₂), or Si(R₂₁)(R₂₂),

R_(2a), R_(2b), R₂₁, and R₂₂ are each independently the same asdescribed in connection with R₂,

R_(3a) and R_(3b) are each independently the same as described inconnection with R₃,

in Formulae CY1-1 to CY1-5, * indicates a binding site to M in Formula1, and *′ indicates a binding site to T₁ in Formula 1,

in Formulae CY2-1 to CY2-5, * indicates a binding site to M in Formula1, *′ indicates a binding site to T₁ in Formula 1, and *″ indicates abinding site to T₂ in Formula 1, and

in Formulae CY3-1 to CY3-6, * indicates a binding site to M in Formula1, *′ indicates a binding site to T₂ in Formula 1, and *″ indicates abinding site to T₃ in Formula 1.

In one or more embodiments, in Formula 1, A₁ may be represented byFormula A1-2, and A₂ may be represented by Formula A2-2.

In one or more embodiments, in Formula 1,

i) A₃ may be represented by Formula A3-1, A₄ may be *—O—*′ or *—S—*′,and T₃ may be *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′,*—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′, or

ii) A₃ may be represented by Formula A3-1, A₄ may be represented by oneof Formulae 4(1) to 4(5), and T₃ may be a single bond, or

iii) A₃ may be represented by Formula A3-2, A₄ may be *—O—*′, or *—S—*′,and T₃ may be a single bond, but embodiments of the present disclosureare not limited thereto.

For example, the organometallic compound represented by Formula 1 may beone of Compounds 1 to 125:

A₄ in Formula 1 may be a first atom linked to M, or a non-cyclic moietyincluding the first atom linked to M, provided that the first atom is B,P, Si, O, or S. Since a moiety contributing to the lowest unoccupiedmolecular orbital (LUMO) energy level in Formula 1 is non-aromatic, itis possible to improve electron transport characteristics of a moietycontributing to the highest occupied molecular orbital (HOMO) energylevel in Formula 1. Thus, electron donating capability of theorganometallic compound may be improved. Therefore, luminescentefficiency of an electronic device, for example, an organiclight-emitting device, which includes the organometallic compound, maybe improved, and an emission wavelength thereof may be easily controlled(for example, an emission wavelength of red light or green light may beobtained).

Also, as described above, Formula 1 satisfies at least one of the “FirstCondition” to the “Third Condition”, and thus, thermal stability andelectron donating capability of the organometallic compound may beimproved by introducing a bicyclic group having a robust structure intothe moiety contributing to the HOMO energy level in Formula 1.Therefore, the lifespan of an electronic device, for example, an organiclight-emitting device, which includes the organometallic compound, maybe improved, and an emission wavelength thereof may be easily controlled(for example, an emission wavelength of red light or green light may beobtained).

For example, HOMO, LUMO, energy band gap (E_(g)), singlet (S₁), andtriplet (T₁) energy levels of some of Compounds illustrated above andCompound A were evaluated by using a DFT method of Gaussian program(structurally optimized at a level of B3LYP, 6-31 G(d,p)).

TABLE 1 Compound HOMO Eg energy S₁ energy T₁ energy No. (eV) LUMO (eV)level (eV) level (eV) level (eV) 1 −4.743 −2.238 2.505 2.155 1.748 16−4.661 −2.245 2.416 2.081 1.703 31 −.4.739 −2.188 2.547 2.193 1.745 46−4.735 −2.139 2.596 2.231 1.743 121 −4.504 −2.156 2.348 2.004 1.621 A−4.482 −2.342 2.140 2.214 1.598

From Table 1, it is confirmed that the organometallic compoundrepresented by Formula 1 has such electrical characteristics that aresuitable for use in an electronic device, for example, for use as adopant for an organic light-emitting device.

Synthesis methods of the organometallic compound represented by Formula1 may be recognizable by one of ordinary skill in the art by referringto Synthesis Examples provided below.

The organometallic compound represented by Formula 1 is suitable for usein an organic layer of an organic light-emitting device, for example,for use as a dopant in an emission layer of the organic layer. Thus,another aspect of the present disclosure provides an organiclight-emitting device that includes:

a first electrode;

a second electrode; and

an organic layer that is disposed between the first electrode and thesecond electrode,

wherein the organic layer includes an emission layer and at least oneorganometallic compound represented by Formula 1.

The organic light-emitting device may have, due to the inclusion of anorganic layer including the organometallic compound represented byFormula 1, a low driving voltage, high efficiency, high power, highquantum efficiency, a long lifespan, a low roll-off ratio, and excellentcolor purity.

The organometallic compound of Formula 1 may be used between a pair ofelectrodes of an organic light-emitting device. For example, theorganometallic compound represented by Formula 1 may be included in theemission layer. In this regard, the organometallic compound may act as adopant, and the emission layer may further include a host (that is, anamount of the organometallic compound represented by Formula 1 issmaller than an amount of the host).

The expression “(an organic layer) includes at least one oforganometallic compounds” as used herein may include an embodiment inwhich “(an organic layer) includes identical organometallic compoundsrepresented by Formula 1” and an embodiment in which “(an organic layer)includes two or more different organometallic compounds represented byFormula 1.”

For example, the organic layer may include, as the organometalliccompound, only Compound 1. In this regard, Compound 1 may be included inan emission layer of the organic light-emitting device. In one or moreembodiments, the organic layer may include, as the organometalliccompound, Compound 1 and Compound 2. In this regard, Compound 1 andCompound 2 may be included in an identical layer (for example, Compound1 and Compound 2 all may be included in an emission layer).

The first electrode may be an anode, which is a hole injectionelectrode, and the second electrode may be a cathode, which is anelectron injection electrode; or the first electrode may be a cathode,which is an electron injection electrode, and the second electrode maybe an anode, which is a hole injection electrode.

In an embodiment, in the organic light-emitting device, the firstelectrode is an anode, the second electrode is a cathode, and theorganic layer further includes a hole transport region disposed betweenthe first electrode and the emission layer and an electron transportregion disposed between the emission layer and the second electrode,wherein the hole transport region includes a hole injection layer, ahole transport layer, an electron blocking layer, or any combinationthereof, and wherein the electron transport region includes a holeblocking layer, an electron transport layer, an electron injectionlayer, or any combination thereof.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers disposed between the first electrode and thesecond electrode of the organic light-emitting device. The “organiclayer” may include, in addition to an organic compound, anorganometallic complex including metal.

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. Hereinafter, the structure of an organiclight-emitting device according to an embodiment and a method ofmanufacturing an organic light-emitting device according to anembodiment will be described in connection with FIG. 1. The organiclight-emitting device 10 includes a first electrode 11, an organic layer15, and a second electrode 19, which are sequentially stacked.

A substrate may be additionally disposed under the first electrode 11 orabove the second electrode 19. As the substrate, any substrate that isused in general organic light-emitting devices may be used, and thesubstrate may be a glass substrate or a transparent plastic substrate,each having excellent mechanical strength, thermal stability,transparency, surface smoothness, ease of handling, and waterresistance.

The first electrode 11 may be formed by depositing or sputtering amaterial for forming the first electrode 11 on the substrate. The firstelectrode 11 may be an anode. The material for forming the firstelectrode 11 may be selected from materials with a high work function tofacilitate hole injection. The first electrode 11 may be a reflectiveelectrode, a semi-transmissive electrode, or a transmissive electrode.The material for forming the first electrode may be, for example, indiumtin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), and zincoxide (ZnO). In one or more embodiments, magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) may be used as the material for forming thefirst electrode.

The first electrode 11 may have a single-layered structure or amulti-layered structure including two or more layers. For example, thefirst electrode 11 may have a three-layered structure of ITO/Ag/ITO, butthe structure of the first electrode 110 is not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emissionlayer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11and the emission layer.

The hole transport region may include a hole injection layer, a holetransport layer, an electron blocking layer, a buffer layer, or anycombination thereof.

The hole transport region may include only either a hole injection layeror a hole transport layer. In one or more embodiments, the holetransport region may have a hole injection layer/hole transport layerstructure or a hole injection layer/hole transport layer/electronblocking layer structure, which are sequentially stacked in this statedorder from the first electrode 11.

A hole injection layer may be formed on the first electrode 11 by usingone or more suitable methods selected from vacuum deposition, spincoating, casting, or Langmuir-Blodgett (LB) deposition.

When a hole injection layer is formed by vacuum deposition, thedeposition conditions may vary depending on a compound that is used toform the hole injection layer, and the structure and thermalcharacteristics of the hole injection layer. For example, the depositionconditions may include a deposition temperature of about 100° C. toabout 500° C., a vacuum pressure of about 10⁻⁸ torr to about 10⁻³ torr,and a deposition rate of about 0.01 Angstroms per second (Å/sec) toabout 100 Å/sec. However, the deposition conditions are not limitedthereto.

When the hole injection layer is formed using spin coating, coatingconditions may vary according to the material used to form the holeinjection layer, and the structure and thermal properties of the holeinjection layer. For example, a coating speed may be from about 2,000revolutions per minute (rpm) to about 5,000 rpm, and a temperature atwhich a heat treatment is performed to remove a solvent after coatingmay be from about 80° C. to about 200° C. However, the coatingconditions are not limited thereto.

Conditions for forming a hole transport layer and an electron blockinglayer may be understood by referring to conditions for forming the holeinjection layer.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzene sulfonic acid (PAN I/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PAN I/CSA),polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound representedby Formula 201 below, and a compound represented by Formula 202 below:

Ar₁₀₁ and Ar₁₀₂ in Formula 201 may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anacenaphthylene group, a fluorenylene group, a phenalenylene group, aphenanthrenylene group, an anthracenylene group, a fluoranthenylenegroup, a triphenylenylene group, a pyrenylene group, a chrysenylenylenegroup, a naphthacenylene group, a picenylene group, a perylenylenegroup, and a pentacenylene group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group.

xa and xb in Formula 201 may each independently be an integer from 0 to5, or may each independently be 0, 1, or 2. For example, xa may be 1 andxb may be 0, but xa and xb are not limited thereto.

R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ in Formulae 201 and 202 mayeach independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group (for example, a methyl group, an ethyl group, apropyl group, a butyl group, a pentyl group, a hexyl group, and so on),and a C₁-C₁₀ alkoxy group (for example, a methoxy group, an ethoxygroup, a propoxy group, a butoxy group, a pentoxy group, and so on);

a C₁-C₁₀ alkyl group and a C₁-C₁₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, and a phosphoric acidgroup or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenylgroup, and a pyrenyl group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group,

but embodiments of the present disclosure are not limited thereto.

R₁₀₉ in Formula 201 may be selected from:

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a alkoxy group, a phenyl group, a naphthyl group, an anthracenylgroup, and a pyridinyl group.

In an embodiment, the compound represented by Formula 201 may berepresented by Formula 201A, but embodiments of the present disclosureare not limited thereto:

R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ in Formula 201A may be understood byreferring to the description provided herein.

For example, the compound represented by Formula 201, and the compoundrepresented by Formula 202 may include compounds HT1 to HT20 illustratedbelow, but are not limited thereto:

A thickness of the hole transport region may be in a range of about 100Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000Å. When the hole transport region includes at least one of a holeinjection layer and a hole transport layer, the thickness of the holeinjection layer may be in a range of about 100 Å to about 10,000 Å, forexample, about 100 Å to about 1,000 Å, and the thickness of the holetransport layer may be in a range of about 50 Å to about 2,000 Å, forexample, about 100 Å to about 1,500 Å. While not wishing to be bound bytheory, it is understood that when the thicknesses of the hole transportregion, the hole injection layer, and the hole transport layer arewithin these ranges, satisfactory hole transporting characteristics maybe obtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments of the presentdisclosure are not limited thereto. Non-limiting examples of thep-dopant are a quinone derivative, such as tetracyanoquinonedimethane(TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane(F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdeniumoxide; and a cyano group-containing compound, such as Compound HT-D1below, but are not limited thereto.

The hole transport region may include a buffer layer.

Also, the buffer layer may compensate for an optical resonance distanceaccording to a wavelength of light emitted from the emission layer, andthus, efficiency of a formed organic light-emitting device may beimproved.

Then, an emission layer may be formed on the hole transport region byvacuum deposition, spin coating, casting, LB deposition, or the like.When the emission layer is formed by vacuum deposition or spin coating,the deposition or coating conditions may be similar to those applied informing the hole injection layer although the deposition or coatingconditions may vary according to a compound that is used to form theemission layer.

Meanwhile, when the hole transport region includes an electron blockinglayer, a material for the electron blocking layer may be selected frommaterials for the hole transport region described above and materialsfor a host to be explained later. However, the material for the electronblocking layer is not limited thereto. For example, when the holetransport region includes an electron blocking layer, a material for theelectron blocking layer may be mCP, which will be explained later.

The emission layer may include a host and a dopant, and the dopant mayinclude the organometallic compound represented by Formula 1.

The host may include at least one selected from TPBi, TBADN, ADN (alsoreferred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, and CompoundH51:

In one or more embodiments, the host may further include a compoundrepresented by Formula 301 below:

Ar₁₁₁ and Ar₁₁₂ in Formula 301 may each independently be selected from:

a phenylene group, a naphthylene group, a phenanthrenylene group, and apyrenylene group; and

a phenylene group, a naphthylene group, a phenanthrenylene group, and apyrenylene group, each substituted with at least one selected from aphenyl group, a naphthyl group, and an anthracenyl group.

Ar₁₁₃ to Ar₁₁₆ in Formula 301 may each independently be selected from:

a C₁-C₁₀ alkyl group, a phenyl group, a naphthyl group, a phenanthrenylgroup, and a pyrenyl group; and

a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenylgroup, each substituted with at least one selected from a phenyl group,a naphthyl group, and an anthracenyl group.

g, h, i, and j in Formula 301 may each independently be an integer from0 to 4, and may each independently be, for example, 0, 1, or 2.

Ar₁₁₃ to Ar₁₁₆ in Formula 301 may each independently be selected from:

a C₁-C₁₀ alkyl group substituted with at least one selected from aphenyl group, a naphthyl group, and an anthracenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group,a phenanthrenyl group, and a fluorenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group,a phenanthrenyl group, and a fluorenyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a alkoxy group, a phenyl group, a naphthyl group,an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and afluorenyl group; and

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, the host may include a compound representedby Formula 302 below:

Ar₁₂₂ to Ar₁₂₅ in Formula 302 are the same as described in detail inconnection with Ar₁₁₃ in Formula 301.

Ar₁₂₆ and Ar₁₂₇ in Formula 302 may each independently be a C₁-C₁₀ alkylgroup (for example, a methyl group, an ethyl group, or a propyl group).

k and l in Formula 302 may each independently be an integer from 0 to 4.For example, k and l may be 0, 1, or 2.

When the organic light-emitting device is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer. Inone or more embodiments, due to a stacked structure including a redemission layer, a green emission layer, and/or a blue emission layer,the emission layer may emit white light.

When the emission layer includes a host and a dopant, an amount of thedopant may be in a range of about 0.01 parts by weight to about 15 partsby weight based on 100 parts by weight of the host, but embodiments ofthe present disclosure are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the emission layer is within this range, excellent light-emissioncharacteristics may be obtained without a substantial increase indriving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.

For example, the electron transport region may have a hole blockinglayer/electron transport layer/electron injection layer structure or anelectron transport layer/electron injection layer structure, but thestructure of the electron transport region is not limited thereto. Theelectron transport layer may have a single-layered structure or amulti-layered structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transportlayer, and the electron injection layer which constitute the electrontransport region may be understood by referring to the conditions forforming the hole injection layer.

When the electron transport region includes a hole blocking layer, thehole blocking layer may include, for example, at least one of BCP,Bphen, and BAlq but embodiments of the present disclosure are notlimited thereto.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1,000 Å, for example, about 30 Å to about 300 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the hole blocking layer is within these ranges, the hole blockinglayer may have improved hole blocking ability without a substantialincrease in driving voltage.

The electron transport layer may further include at least one selectedfrom BCP, Bphen, Alq₃, BAlq, TAZ, and NTAZ.

In one or more embodiments, the electron transport layer may include atleast one of ET1 and ET25, but are not limited thereto:

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whilenot wishing to be bound by theory, it is understood that when thethickness of the electron transport layer is within the range describedabove, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

Also, the electron transport layer may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium quinolate, LiQ) orET-D2:

The electron transport region may include an electron injection layerthat promotes flow of electrons from the second electrode 19 thereinto.

The electron injection layer may include at least one selected from LiF,NaCl, CsF, Li₂O, and BaO.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. While notwishing to be bound by theory, it is understood that when the thicknessof the electron injection layer is within the range described above, theelectron injection layer may have satisfactory electron injectioncharacteristics without a substantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The secondelectrode 19 may be a cathode. A material for forming the secondelectrode 19 may be selected from metal, an alloy, an electricallyconductive compound, and a combination thereof, which have a relativelylow work function. For example, lithium (Li), magnesium (Mg), aluminum(Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),or magnesium-silver (Mg—Ag) may be used as a material for forming thesecond electrode 19. In one or more embodiments, to manufacture atop-emission type light-emitting device, a transmissive electrode formedusing ITO or IZO may be used as the second electrode 19.

Hereinbefore, the organic light-emitting device has been described withreference to FIG. 1, but embodiments of the present disclosure are notlimited thereto.

Another aspect of the present disclosure provides a diagnosticcomposition including at least one organometallic compound representedby Formula 1.

The organometallic compound represented by Formula 1 provides highluminescent efficiency. Accordingly, a diagnostic composition includingthe organometallic compound may have high diagnostic efficiency.

The diagnostic composition may be used in various applications includinga diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched saturated aliphatic hydrocarbon monovalent group having 1 to 60carbon atoms, and non-limiting examples thereof include a methyl group,an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₆₀ alkyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and non-limiting examples thereof include a methoxy group, an ethoxygroup, and an iso-propyloxy group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup formed by including at least one carbon-carbon double bond in themiddle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof include an ethenyl group, a propenyl group, and a butenyl group.The term “C₂-C₆₀ alkenylene group” as used herein refers to a divalentgroup having the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup formed by including at least one carbon-carbon triple bond in themiddle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof include an ethynyl group, and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein refers to a divalent group having thesame structure as the C₂-C₆₀ alkynyl group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andnon-limiting examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group” as used herein refers to adivalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent saturated monocyclic group having at least one heteroatomselected from N, O, P, Si and S as a ring-forming atom and 1 to 10carbon atoms, and non-limiting examples thereof include atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₁₀ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and that has noaromaticity, and non-limiting examples thereof include a cyclopentenylgroup, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group havingthe same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one carbon-carbon double bond in its ring. Examples of theC₁-C₁₀ heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having the samestructure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, andthe term “C₆—C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms.Non-limiting examples of the C₆-C₆₀ aryl group include a phenyl group, anaphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenylgroup, and a chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀arylene group each include two or more rings, the rings may be fused toeach other.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a carbocyclic aromatic system that has at least oneheteroatom selected from N, O, P, Si, and S as a ring-forming atom, and1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group” as usedherein refers to a divalent group having a carbocyclic aromatic systemthat has at least one heteroatom selected from N, O, P, and S as aring-forming atom, and 1 to 60 carbon atoms. Non-limiting examples ofthe C₁-C₆₀ heteroaryl group include a pyridinyl group, a pyrimidinylgroup, a pyrazinyl group, a pyridazinyl group, a triazinyl group, aquinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀ heteroarylgroup and the C₁-C₆₀ heteroarylene group each include two or more rings,the rings may be fused to each other.

The term “C₆-C₆₀ aryloxy group” as used herein indicates —OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group as usedherein indicates —SA₁₀₃ (wherein A103 is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed to each other, only carbonatoms as ring-forming atoms, and no aromaticity in its entire molecularstructure. Examples of the monovalent non-aromatic condensed polycyclicgroup include a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedpolycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 2 to 60carbon atoms) having two or more rings condensed to each other, aheteroatom selected from N, O, P, Si, and S, other than carbon atoms, asa ring-forming atom, and no aromaticity in its entire molecularstructure. Non-limiting examples of the monovalent non-aromaticcondensed heteropolycyclic group include a carbazolyl group. The term“divalent non-aromatic condensed heteropolycyclic group” as used hereinrefers to a divalent group having the same structure as the monovalentnon-aromatic condensed heteropolycyclic group.

The term “C₅-C₃₀ carbocyclic group” as used herein refers to a saturatedor unsaturated cyclic group having, as a ring-forming atom, 5 to 30carbon atoms only. The C₅-C₃₀ carbocyclic group may be a monocyclicgroup or a polycyclic group.

The term “C₁-C₃₀ heterocyclic group” as used herein refers to asaturated or unsaturated cyclic group having, as a ring-forming atom, atleast one heteroatom selected from N, O, Si, P, and S other than 1 to 30carbon atoms. The C₁-C₃₀ heterocyclic group may be a monocyclic group ora polycyclic group.

At least one substituent of the substituted C₅-C₃₀ carbocyclic group,the substituted C₂-C₃₀ heterocyclic group, the substituted C₅-C₃₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁—C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅),—B(Q₁₆)(Q₁₇), and —P(═O)(Q₁₈)(Q₁₉);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,—CD3, -CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃—C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅),—B(Q₂₆)(Q₂₇), and —P(═O)(Q₂₈)(Q₂₉); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), and —P(═O)(Q₃₈)(Q₃₉),and

Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryl groupsubstituted with at least one selected from a C₁—C₆₀ alkyl group and aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group.

When a group containing a specified number of carbon atoms issubstituted with any of the groups listed in the preceding paragraph,the number of carbon atoms in the resulting “substituted” group isdefined as the sum of the carbon atoms contained in the original(unsubstituted) group and the carbon atoms (if any) contained in thesubstituent. For example, when the term “substituted C₁-C₃₀ alkyl”refers to a C₁-C₃₀ alkyl group substituted with C₆-C₃₀ aryl group, thetotal number of carbon atoms in the resulting aryl substituted alkylgroup is C₇-C₆₀.

Hereinafter, a compound and an organic light-emitting device accordingto embodiments are described in detail with reference to SynthesisExample and Examples. However, the organic light-emitting device is notlimited thereto. The wording “B was used instead of A” used indescribing Synthesis Examples means that an amount of A used wasidentical to an amount of B used, in terms of a molar equivalent.

EXAMPLES Synthesis Example 1 Synthesis of Compound 1

Synthesis of Intermediate 1-1

10.00 grams (g) (18.20 millimoles, mmol) of the starting material 1a(1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole),8.00 g (36.30 mmol) of di-tert-butyl dicarbonate, 4.40 g (36.30 mmol) of4-dimethylaminopyridine, and 50 milliliters (mL) of triethylamine wereadded to a 500-mL round-bottom flask with a stirrer in a nitrogenatmosphere, and heated under reflux for 24 hours. After the reaction wascompleted, the organic layer was extracted with 400 mL ofdichloromethane, washed with a NaCl aqueous solution (100 mL×2), driedwith MgSO₄, and filtered. The solvent was distilled off under reducedpressure. The resulting residue was purified by column chromatography(ethyl acetate/hexane=1:10) to obtain 11.5 g (yield: 99%) ofIntermediate 1-1. The obtained compound was identified by LC-MS.

LC-MS m/z=651.65 (M+H)⁺.

Synthesis of Intermediate 1-2

14.0 g (21.5 mmol) of Intermediate 1-1 (tert-butyl1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole-9-carboxylate)and 8.2 g (32.3 mmol) of bis(pinacolato)diboron were added to a flask,and 500 mL of toluene was added thereto in a nitrogen atmosphere. Then,1.0 g (1.2 mmol) of PdCl₂(dppf) and 6.3 g (64.6 mmol) of KOAc weresequentially added thereto, and the reaction mixture was stirred at atemperature of 110° C. for 24 hours. After the reaction was completed,the reaction product was cooled to room temperature, and toluene wasdistilled off under reduced pressure. Then, 500 mL of ethyl acetate wasadded to the residue. The organic layer obtained therefrom was washedwith a saturated NaHCO₃ aqueous solution (150 mL×2) and a saturated NaClaqueous solution (100 mL×2), dried with MgSO₄, and filtered. The solventwas distilled off under reduced pressure. The resulting residue waspurified by column chromatography (ethyl acetate/hexane=1:20) to obtain5.0 g (yield: 33%) of Intermediate 1-2. The obtained compound wasidentified by LC-MS.

LC-MS m/z=698.71 (M+H)⁺.

Synthesis of Intermediate 1-3

5.3 g (7.64 mmol) of Intermediate 1-2 (tert-butyl3,6-di-tert-butyl-1-(1-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-benzo[d]imidazole-2-yl)-9H-carbazole-9-carboxylate)and 1.5 g (6.94 mmol) of methyl 6-bromopicolinate were added to a flask,and 150 ml of a mixed solvent of tetrahydrofuran/distilled water (4:1)was added thereto in a nitrogen atmosphere. Then, 0.4 g (0.35 mmol) oftetrakis(triphenylphospine)palladium(0) and 2.21 g (20.83 mmol) ofpotassium carbonate were sequentially added thereto, and the reactionmixture was stirred at a temperature of 110° C. for 24 hours. After thereaction was completed, the reaction product was cooled to roomtemperature and 500 mL of ethyl acetate was added thereto. The organiclayer obtained therefrom was washed with a saturated NaHCO₃ aqueoussolution (150 mL×2) and a saturated NaCl aqueous solution (100 mL×2),dried with MgSO₄, and filtered. The solvent was distilled off underreduced pressure. The resulting residue was purified by columnchromatography (ethyl acetate/hexane=1:20) to obtain 2.3 g (yield: 47%)of Intermediate 1-3. The obtained compound was identified by LC-MS.

LC-MS m/z=707.87 (M+H)⁺.

Synthesis of Intermediate 1-4

3.5 g of Intermediate 1-3 (tert-butyl3,6-di-tert-butyl-1-(4-(6-(methoxycarbonyl)pyridine-2-yl)-1-phenyl-1H-benzo[d]imidazole-2-yl)-9H-carbazole-9-carboxylate)was mixed with 20 mL of tetrahydrofuran at room temperature, and 0.2 gof lithium hydroxide mixed with 2 mL of distilled water were addedthereto. The resulting mixture was stirred at room temperature for 5hours. After the reaction was completed, 500 mL of ethyl acetate wasadded to the reaction product. The organic layer obtained therefrom waswashed with a saturated NaHCO₃ aqueous solution (150 mL×2) and asaturated NaCl aqueous solution (100 mL×2), dried with MgSO₄, andfiltered. The solvent was distilled off under reduced pressure. Theresulting residue was purified by column chromatography (ethylacetate/hexane=1:5) to obtain 3.3 g (yield: 99%) of Intermediate 1-4.The obtained compound was identified by LC-MS.

LC-MS m/z=693.84 (M+H)⁺.

Synthesis of Intermediate 1-5

3.0 g (23.3 mmol) of Intermediate 1-4(6-(2-(9-(tert-butoxycarbonyl)-3,6-di-tert-butyl-9H-carbazole-1-yl)-1-phenyl-1H-benzo[d]imidazole-4-yl)picolinicacid) was mixed with 50 mL of dichloromethane, and 1.0 mL oftrifluoroacetic acid was slowly added dropwise thereto. The resultingmixture was stirred at a temperature of 100° C. for 12 hours. After thereaction was completed, a distillation process was performed on thereaction product under reduced pressure to remove dichloromethane andtrifluoroacetic acid therefrom, and 300 mL of ethyl acetate was addedthereto. Then, a saturated NaHCO₃ aqueous solution was added to anorganic layer obtained therefrom until neutralized (pH=7 to 8), and theorganic layer was separated therefrom. The obtained organic layer waswashed with a saturated NaCl aqueous solution (100 mL×2), dried withMgSO₄, and filtered. The solvent was distilled off under reducedpressure to obtain 2.3 g (yield: 78%) of Intermediate 1-5. The obtainedcompound was identified by LC-MS.

LC-MS m/z=593.73 (M+H)⁺.

Synthesis of Compound 1

2.0 g (5.06 mmol) of Intermediate 1-5(6-(2-(3,6-di-tert-butyl-9H-carbazole-1-yl)-1-phenyl-1H-benzo[d]imidazole-4-yl)picolinicacid) and 2.52 g (6.07 mmol) of K₂PtCl₄ were mixed with 70 mL of a mixedsolvent including 60 mL of AcOH and 10 mL of H₂O, and the resultingmixture was refluxed for 16 hours. The resulting mixture was cooled toroom temperature, and a precipitate was filtered therefrom. Theprecipitate was dissolved again in methylene chloride (MC) and washedwith H₂O. The crude product was purified by column chromatography (MC30%, Hex 70%) to obtain 1.50 g (yield: 38%) of Compound 1. The obtainedcompound was identified by LC-MS.

LC-MS m/z=786.80 (M+H)⁺.

Synthesis Example 2 Synthesis of Compound 16

1.1 g (yield: 41%) of Compound 16 was synthesized in the same manner asin Synthesis Example 1, except that the starting material 16a was usedinstead of the starting material 1 a(1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole)in synthesizing Intermediate 1-1. The obtained compound was identifiedby LC-MS.

LC-MS m/z=674.58 (M+H)⁺.

Synthesis Example 3 Synthesis of Compound 31

0.8 g (yield: 32%) of Compound 31 was synthesized in the same manner asin Synthesis Example 1, except that 2-bromoquinoline-8-ol was usedinstead of methyl 6-bromopicolinate in synthesizing Intermediate 1-3.The obtained compound was identified by LC-MS.

LC-MS m/z=808.85 (M+H)⁺.

Synthesis Example 4 Synthesis of Compound 46

1.0 g (yield: 35%) of Compound 46 was synthesized in the same manner asin Synthesis Example 1, except that the starting material 16a was usedinstead of the starting material 1 a(1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole)in synthesizing Intermediate 1-1, and 2-bromoquinoline-8-ol was usedinstead of methyl 6-bromopicolinate in synthesizing Intermediate 1-3.The obtained compound was identified by LC-MS.

LC-MS m/z=696.63 (M+H)⁺.

Synthesis Example 5 Synthesis of Compound 61

0.7 g (yield: 30%) of Compound 61 was synthesized in the same manner asin Synthesis Example 1, except that the starting material 61a(4-bromo-2-(5-(tert-butyl)-1H-indole-7-yl)-1-phenyl-1H-benzo[d]imidazole)was used instead of the starting material 1a(1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole)in synthesizing Intermediate 1-1. The obtained compound was identifiedby LC-MS.

LC-MS m/z=680.63 (M+H)⁺.

Synthesis Example 6 Synthesis of Compound 91

0.9 g (yield: 31%) of Compound 91 was synthesized in the same manner asin Synthesis Example 1, except that the starting material 61a(4-bromo-2-(5-(tert-butyl)-1H-indole-7-yl)-1-phenyl-1H-benzo[d]imidazole)was used instead of the starting material 1a(1-(4-bromo-1-phenyl-1H-benzo[d]imidazole-2-yl)-3,6-di-tert-butyl-9H-carbazole)in synthesizing Intermediate 1-1, and 2-bromoquinoline-8-ol was usedinstead of methyl 6-bromopicolinate in synthesizing Intermediate 1-3.The obtained compound was identified by LC-MS.

LC-MS m/z=702.68 (M+H)⁺.

Evaluation Example 1 Evaluation of Photoluminescence Quantum Yield(PLQY)

A CH₂Cl₂ solution of polymethyl methacrylate (PMMA) and a mixture of 8percent by weight (wt%) of CBP and Compound 1 (an amount of Compound 1was 10 parts by weight based on 100 parts by weight of the mixture) weremixed. The resulting mixture was coated on a quartz substrate by using aspin coater, thermally treated at a temperature of 80° C. in an oven,and then coated to room temperature, thereby completing the manufactureof film 1.

The luminescence quantum yield of film 1 was evaluated by using aHamamatsu Photonics absolute photoluminescence (PL) quantum yieldmeasurement system equipped with a xenon light source, a monochromator,a photonic multichannel analyzer, and an integrating sphere, andphotoluminescence quantum yield (PLQY) measurement software (HamamatsuPhotonics, Ltd., Shizuoka, Japan). It was confirmed from the evaluationresult that the PLQY in film of Compound 1 was 0.998. Therefore, it isconfirmed that Compound 1 has high PLQY in film.

Example 1

As an anode, a glass substrate, on which ITO/Ag/ITO were respectivelydeposited to thicknesses of 70 Angstroms (Å)/1,000 Å/70 Å, was cut to asize 50 mm×50 mm×0.5 mm (mm=millimeter), sonicated with iso-propylalcohol and pure water each for 5 minutes, and then cleaned by exposureto ultraviolet rays and ozone for 30 minutes. Then, the resulting glasssubstrate was provided to a vacuum deposition apparatus.

2-TNATA was deposited on the anode to form a hole injection layer havinga thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(NPB) was deposited on the hole injection layer to form a hole transportlayer having a thickness of 1,350 Å.

CBP (host) and Compound 1 (dopant) were co-deposited on the holetransport layer at a weight ratio of 94:6 to form an emission layerhaving a thickness of 400 Å, and BCP was deposited on the emission layerto form a hole blocking layer having a thickness of 50 Å. Then, Alq₃ wasdeposited on the hole blocking layer to form an electron transport layerhaving a thickness of 350 Å, LiF was deposited on the electron transportlayer to form an electron injection layer having a thickness of 10 Å,and MgAg was deposited on the electron injection layer at a weight ratioof 90:10 to form a cathode having a thickness of 120 Å, therebycompleting the manufacture of an organic light-emitting device (emittingred light) having a structure of ITO/Ag/ITO/2-TNATA (600 Å)/NPB (1,350Å)/CBP+Compound 1 (6 wt %) (400 Å)/BCP (50 Å)/Alq₃ (350 Å)/LiF (10Å)/MgAg (120 Å).

Examples 2 to 5 and Comparative Example A

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that Compounds shown in Table 2 were each usedinstead of Compound 1 as a dopant in forming an emission layer.

Evaluation Example 2 Evaluation of Characteristics of OrganicLight-Emitting Devices

The driving voltage, luminescent efficiency, and PLQY of the organiclight-emitting devices manufactured according to Examples 1 to 5 andComparative Example A were evaluated, and evaluation results thereof areshown in Table 2. This evaluation was performed using a current-voltagemeter (Keithley 2400) and a luminance meter (Minolta Cs-1,000A).

TABLE 2 Driving Luminescent voltage efficiency Dopant (V) (cd/A) PLQY(%) Example 1 Compound 4.892 17.34 14.85  1 Example 2 Compound 4.88318.15 15.32 16 Example 3 Compound 5.001 19.88 17.24 46 Example 4Compound 4.913 18.33 15.20 61 Example 5 Compound 5.000 18.92 15.92 91Comparative Compound 5.421 14.35 12.22 Example A A

Referring to Table 2, it is confirmed that the organic light-emittingdevices of Examples 1 to 5 have excellent or equivalent driving voltage,luminescent efficiency, and PLQY characteristics, as compared with thoseof the organic light-emitting device of Comparative Example A.

As described above, the organometallic compounds according to theembodiments of the present disclosure have excellent electricalcharacteristics and thermal stability, and accordingly, organiclight-emitting devices including such organometallic compounds may haveexcellent driving voltage, efficiency, power, color purity, and lifespancharacteristics. Also, due to excellent phosphorescent luminescencecharacteristics, such organometallic compounds may provide a diagnosticcomposition having high diagnostic efficiency.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

While one or more embodiments have been described with reference to thefigures, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope of the present disclosure as definedby the following claims.

What is claimed is:
 1. An organometallic compound represented by Formula1: Formula 1

wherein M in Formula 1 is beryllium (Be), magnesium (Mg), aluminum (Al),calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu),zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru),rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt),or gold (Au), in Formula 1, two bonds selected from a bond between A₁and M, a bond between A₂ and M, a bond between A₃ and M, and a bondbetween A₄ and M are each a covalent bond, and the others thereof areeach a coordinate bond, A₁ in Formula 1 is ring CY₁ represented byFormula A1-1 or A1-2, and in Formulae A1-1 and A1-2, * indicates abinding site to M in Formula 1, and *′ indicates a binding site to T₁ inFormula 1, A₂ in Formula 1 is ring CY₂ represented by one of FormulaeA2-1 to A2-3, and in Formulae A2-1 to A2-3, * indicates a binding siteto M in Formula 1, *′ indicates a binding site to T₁ in Formula 1, and*″ indicates a binding site to T₂ in Formula 1, A₃ in Formula 1 is ringCY₃ represented by one of Formulae A3-1 to A3-3, and in Formulae A3-1 toA3-3, * indicates a binding site to M in Formula 1, *″ indicates abinding site to T₂ in Formula 1, and *′ indicates a binding site to T₃in Formula 1, A₄ in Formula 1 is a first atom linked to M, or anon-cyclic moiety comprising the first atom linked to M, the first atomis B, P, Si, O, or S, X₁ to X₃ and Y₁ to Y₆ in Formulae A1-1, A1-2, A2-1to A2-3, and A3-1 to A3-3 are each independently C or N, rings CY₁ toCY₃ in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1 to A3-3 are eachindependently a C₅-C₃₀ carbocyclic group or a C₁-C₃₀ heterocyclic group,in Formula 1, T₁ to T₃ are each independently selected from a singlebond, a double bond, *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′,*—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′,*—S(═O)—*′, *—S(═O)₂-*′, *—C(R₇)═*′, *═C(R₇)—*′, *—C(R₇)═C(R₈)—*′,*—C(═O)—*′, and *—C≡C—*′, and * and *′ each indicate a binding site to aneighboring atom, R₇ and R₈ are optionally linked via a single bond, adouble bond, or a first linking group to form a substituted orunsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstitutedC₁-C₃₀ heterocyclic group, R₁ to R₃, R₇, and R₈ are each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and—P(═O)(Q₈)(Q₉), a1 to a3 in Formulae A1-1, A1-2, A2-1 to A2-3, and A3-1to A3-3 are each independently an integer from 0 to 20, two of aplurality of neighboring groups R₁ are optionally linked to form asubstituted or unsubstituted C₅-C₃₀ carbocyclic group or a substitutedor unsubstituted C₁-C₃₀ heterocyclic group, two of a plurality ofneighboring groups R₂ are optionally linked to form a substituted orunsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstitutedC₁-C₃₀ heterocyclic group, two of a plurality of neighboring groups R₃are optionally linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup, two or more groups selected from R₁ to R₃ are optionally linkedto form a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₃₀ heterocyclic group, A₁ and A₄ inFormula 1 are not linked to each other, Formula 1 satisfies at least oneof a “First Condition” to a “Third Condition”: “First Condition” A₁ inFormula 1 is represented by Formula A1-2, “Second Condition” A₂ inFormula 1 is represented by Formula A2-2 or A2-3, and “Third Condition”A₃ in Formula 1 is represented by Formula A3-2 or A3-3, at least onesubstituent of the substituted C₅-C₃₀ carbocyclic group, the substitutedC₁-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group is selected from: deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, and a C₁—C₆₀ alkoxy group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, 13CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅),—B(Q₁₆)(Q₁₇), and —P(═O)(Q₁₈)(Q₁₉); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group; a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁—C₆₀ alkyl group, a C₂-C₆₀ alkenylgroup, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅),—B(Q₂₆)(Q₂₇), and —P(═O)(Q₂₈)(Q₂₉); and —N(Q₃₁)(Q₃₂),—Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), and —P(═O)(Q₃₈)(Q₃₉), and Q₁ to Q₉,Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ are each independently selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₁-C₆₀ alkyl group substituted with at least one selectedfrom deuterium, a C₁-C₆₀ alkyl group, and a C₆-C₆₀ aryl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryl group substituted with at least one selected from deuterium, aC₁-C₆₀ alkyl group, and a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆—C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group.
 2. The organometallic compound ofclaim 1, wherein the bond between A₁ and M and the bond between A₄ and Mare each a covalent bond, and the bond between A₂ and M and the bondbetween A₃ and M are each a coordinate bond.
 3. The organometalliccompound of claim 1, wherein the first atom is O.
 4. The organometalliccompound of claim 1, wherein rings CY₁ to CY₃ are each independentlyselected from a benzene group, a naphthalene group, an anthracene group,a phenanthrene group, a triphenylene group, a pyrene group, a chrysenegroup, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, afuran group, a thiophene group, a silole group, an indene group, afluorene group, an indole group, a carbazole group, a benzofuran group,a dibenzofuran group, a benzothiophene group, a dibenzothiophene group,a benzosilole group, a dibenzosilole group, an azafluorene group, anazacarbazole group, an azadibenzofuran group, an azadibenzothiophenegroup, an azadibenzosilole group, a pyridine group, a pyrimidine group,a pyrazine group, a pyridazine group, a triazine group, a quinolinegroup, an isoquinoline group, a quinoxaline group, a quinazoline group,a phenanthroline group, a pyrrole group, a pyrazole group, an imidazolegroup, a triazole group, an oxazole group, an isoxazole group, athiazole group, an isothiazole group, an oxadiazole group, a thiadiazolegroup, a benzopyrazole group, a benzimidazole group, a benzoxazolegroup, a benzothiazole group, a benzoxadiazole group, a benzothiadiazolegroup, a 5,6,7,8-tetrahydroisoquinoline group, a5,6,7,8-tetrahydroquinoline group, and a benzocarbazole group.
 5. Theorganometallic compound of claim 1, wherein at least one of rings CY₁ toCY₃ is a condensed ring with two or more 6-membered rings or a condensedring with at least one 5-membered ring and at least one 6-membered ring,the 5-membered ring is selected from a cyclopentadiene group, a furangroup, a thiophene group, a pyrrole group, a silole group, an oxazolegroup, an isoxazole group, an oxadiazole group, an isoxadiazole group,an oxatriazole group, an isoxatriazole group, a thiazole group, anisothiazole group, a thiadiazole group, an isothiadiazole group, athiatriazole group, an isothiatriazole group, a pyrazole group, animidazole group, a triazole group, a tetrazole group, an azasilolegroup, a diazasilole group, and a triazasilole group, and the 6-memberedring is selected from a cyclohexane group, a cyclohexene group, anadamantane group, a norbornane group, a norbornene group, a benzenegroup, a pyridine group, a pyrimidine group, a pyrazine group, apyridazine group, and a triazine group.
 6. The organometallic compoundof claim 1, wherein R₁ to R₃, R₇, and R₈ are each independently selectedfrom: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, —SF₅, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group; a C₁-C₂₀alkyl group and a C₁-C₂₀ alkoxy group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃,—CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkylgroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group; a cyclopentyl group, a cyclohexyl group,a cycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a pyrrolyl group, a thiophenyl group, a furanyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolylgroup, an indolyl group, an indazolyl group, a purinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group; a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbomenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,—CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, an imidazopyridinyl group, an imidazopyrimidinyl group, and—Si(Q₃₃)(Q₃₄)(Q₃₅); and —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and—P(═O)(Q₈)(Q₉), and Q₁ to Q₉ and Q₃₃ to Q₃₅ are each independentlyselected from: —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H,—CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, and—CD₂CDH₂; an n-propyl group, an iso-propyl group, an n-butyl group, aniso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, aphenyl group, and a naphthyl group; and an n-propyl group, an iso-propylgroup, an n-butyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentylgroup, a tert-pentyl group, a phenyl group, and a naphthyl group, eachsubstituted with at least one selected from deuterium, a C₁-C₁₀ alkylgroup, and a phenyl group.
 7. The organometallic compound of claim 1,wherein R₁ to R₃, R₇, and R₈ are each independently selected fromhydrogen, deuterium, —F, a cyano group, a nitro group, —SF₅, —CH₃, —CD₃,—CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, groups represented by Formulae 9-1 to9-19, groups represented by Formulae 10-1 to 10-156, -N(Q₁)(Q₂),—Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉):

wherein, in Formulae 9-1 to 9-19 and 10-1 to 10-156, “Ph” indicates aphenyl group, “TMS” indicates a trimethylsilyl group, and “*” indicatesa binding site to a neighboring atom.
 8. The organometallic compound ofclaim 1, wherein A₁ is represented by one of Formulae A1-1(1) toA1-1(26) and A1-2(1) to A1-2(74):

wherein, in Formulae A1-1(1) to A1-1(26) and A1-2(1) to A1-2(74), X₁ andR₁ are each independently the same as in claim 1, X₁₁ is O, S, N(R₁₁),C(R₁₁)(R₁₂), or Si(R₁₁)(R₁₂), X₁₃ is N or C(R₁₃), X₁₄ is N or C(R₁₄),R₁₁ to R₁₈ are each independently the same as R₁ in claim 1, a17 is aninteger from 0 to 7, a16 is an integer from 0 to 6, a15 is an integerfrom 0 to 5, a14 is an integer from 0 to 4, a13 is an integer from 0 to3, a12 is an integer from 0 to 2, * indicates a binding site to M inFormula 1, and *′ indicates a binding site to T₁ in Formula
 1. 9. Theorganometallic compound of claim 1, wherein A₂ is represented by one ofFormulae A2-1(1) to A2-1(17), A2-2(1) to A2-2(58), and A2-3(1) toA2-3(58):

wherein, in Formulae A2-1(1) to A2-1(17), A2-2(1) to A2-2(58), andA2-3(1) to A2-3(58), X₂ and R₂ are each independently the same as inclaim 1, X₂₁ is O, S, N(R₂₁), C(R₂₁)(R₂₂), or Si(R₂₁)(R₂₂), X₂₃ is N orC(R₂₃), X₂₄ is N or C(R₂₄), R₂₁ to R₂₈ are each independently the sameas R₂ in claim 1, a26 is an integer from 0 to 6, a25 is an integer from0 to 5, a24 is an integer from 0 to 4, a23 is an integer from 0 to 3,a22 is an integer from 0 to 2, * indicates a binding site to M inFormula 1, *′ indicates a binding site to T₁ in Formula 1, and *″indicates a binding site to T₂ in Formula
 1. 10. The organometalliccompound of claim 1, wherein A₃ is represented by one of FormulaeA3-1(1) to A3-1(21), A3-2(1) to A3-2(58), and A3-3(1) to A3-3(58):

wherein, in Formulae A3-1(1) to A3-1(21), A3-2(1) to A3-2(58), andA3-3(1) to A3-3(58), X₃ and R₃ are each independently the same as inclaim 1, X₃₁ is O, S, N(R₃₁), C(R₃₁)(R₃₂), or Si(R₃₁)(R₃₂), X₃₃ is N orC(R₃₃), X₃₄ is N or C(R₃₄), R₃₁ to R₃₈ are each independently the sameas R₃ in claim 1, a36 is an integer from 0 to 6, a35 is an integer from0 to 5, a34 is an integer from 0 to 4, a33 is an integer from 0 to 3,a32 is an integer from 0 to 2, * indicates a binding site to M inFormula 1, *″ indicates a binding site to T₂ in Formula 1, and *′indicates a binding site to T₃ in Formula
 1. 11. The organometalliccompound of claim 1, wherein i) A₄ is *—O—*′, or *—S—*′, and T₃ is*—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′, *—Si(R₇)(R₈)—*′,*—Ge(R₇)(R₈)—*′, or *—C(═O)—*′; ii) A₄ is represented by one of Formulae4(1) to 4(5), and T₃ is a single bond, or iii) A₄ is *—O—*′, or *—S—*′,and T₃ is a single bond:

wherein, in Formulae A4(1) to A4(5), R₄₁ and R₄₂ are each independentlythe same as R₁ in claim 1, * indicates a binding site to M in Formula 1,and *′ indicates a binding site to T₃ in Formula
 1. 12. Theorganometallic compound of claim 1, wherein A₁ is represented by one ofFormulae CY1-1 to CY1-11, A₂ is represented by one of Formulae CY2-1 toCY2-5, and A₃ is represented by one of Formulae CY3-1 to CY3-10:

wherein, in Formulae CY1-1 to CY1-11, CY2-1 to CY2-5, and CY3-1 toCY3-10, X₂, X₃, and R₁ to R₃ are each independently the same as in claim1, R_(1a) and R_(1b) are each independently the same as R₁ in claim 1,X₂₁ is O, S, N(R₂₁), C(R₂₁)(R₂₂), or Si(R₂₁)(R₂₂), R_(2a), R_(2b), R₂₁,and R₂₂ are each independently the same as R₂ in claim 1, R_(3a) andR_(3b) are each independently the same as R₃ in claim 1, in FormulaeCY1-1 to CY1-5, * indicates a binding site to M in Formula 1, and *′indicates a binding site to T₁ in Formula 1, in Formulae CY2-1 toCY2-5, * indicates a binding site to M in Formula 1, *′ indicates abinding site to T₁ in Formula 1, and *″ indicates a binding site to T₂in Formula 1, and in Formulae CY3-1 to CY3-6, * indicates a binding siteto M in Formula 1, *″ indicates a binding site to T₂ in Formula 1, and*″ indicates a binding site to T₃ in Formula
 1. 13. The organometalliccompound of claim 1, wherein A₁ is represented by Formula A1-2, and A2is represented by Formula A2-2.
 14. The organometallic compound of claim1, wherein i) A₃ is represented by Formula A3-1, A₄ is *—O—*′, or*—S—*′, T₃ is *—N(R₇)—*′, *—B(R₇)—*′, *—P(R₇)—*′, *—C(R₇)(R₈)—*′,*—Si(R₇)(R₈)—*′, *—Ge(R₇)(R₈)—*′, or *—C(═O)—*′, ii) A₃ is representedby Formula A3-1, A₄ is represented by one of Formulae 4(1) to 4(5), andT₃ is a single bond, or, iii) A₃ is represented by Formula A3-2, A₄ is*—O—*′, or *—S—*′, and T₃ is a single bond:

wherein, in Formulae A4(1) to A4(5), R₄₁ and R₄₂ are each independentlythe same as R₁ in claim 1, * indicates a binding site to M in Formula 1,and *′ indicates a binding site to T₃ in Formula
 1. 15. Theorganometallic compound of claim 1, wherein the organometallic compoundis one of Compounds 1 to 125:


16. An organic light-emitting device comprising: a first electrode; asecond electrode; and an organic layer disposed between the firstelectrode and the second electrode and comprising an emission layer,wherein the organic layer comprises at least one organometallic compoundof claim
 1. 17. The organic light-emitting device of claim 16, whereinthe first electrode is an anode, the second electrode is a cathode, andthe organic layer further comprises a hole transport region disposedbetween the first electrode and the emission layer and an electrontransport region disposed between the emission layer and the secondelectrode, wherein the hole transport region comprises a hole injectionlayer, a hole transport layer, an electron blocking layer, or anycombination thereof, and wherein the electron transport region comprisesa hole blocking layer, an electron transport layer, an electroninjection layer, or any combination thereof.
 18. The organiclight-emitting device of claim 16, wherein the emission layer comprisesthe organometallic compound.
 19. The organic light-emitting device ofclaim 18, wherein the emission layer further comprises a host, andwherein an amount of the host is larger than an amount of theorganometallic compound.
 20. A diagnostic composition comprising theorganometallic compound of claim 1.